How it works: “Drop is a mobile rewards program tied to your debit and credit cards. You earn points taking an Uber or using Wealthsimple, for example, and use them at places such as ­Starbucks or on Amazon.”

How much you spent initially: “I had built a business before, so my clients had a lot of trust in me. I raised $1 million off a PowerPoint deck, essentially.”

Past life: “I was an intern at Microsoft at 18, spent two years on the Bay Street trading floor, worked at Merrill Lynch during the collapse, and was at the Clinton Foundation back when the Clintons and Trumps were friends.”

The best advice you’ve received: “It all starts from the top. The CEO sets a company’s culture, work ethic and tone, because everyone is looking up to you.”

The worst advice you’ve received: “That you need to bootstrap until you’re profitable. Would Uber and Airbnb have been able to bootstrap?”

Eureka moment: “After I sold my first company, a music platform called Tunezy, one of my clients told me they wanted to reach millennials with a loyalty rewards program. I came up with the idea for Drop when I noticed big players like Aeroplan and Air Miles were outdated, because they were created when the world was a completely different place, without the Internet or smartphones.”

Tech jargon you use too much: “Data science.”

Tech jargon you hate: “AI—companies tack it onto everything because they think it looks cool.”

Your tech role model: “Richard Branson. I admire his boldness and ambition. He’s not scared to jump into industries that are completely unknown to him.”

App you can’t live without: “MyFitnessPal. I’m into weightlifting, and I use it to track calories.”

If you weren’t running a start-up: “I trained at the Royal Conservatory, so I’d be a musician—a Jack Johnson or John Mayer type.”

Coolest thing in your office: “Jamie, the office dog. He’s a pug–beagle–shih tzu mix named after Jameson whiskey, born the day Drop was incorporated.”